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Winning With Women Wednesday: An Interview with Tara Cunningham, Director of Strategic Planning, Jay & Linda Grunin Foundation

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Tara Liston Cunningham

It’s Winning With Women Wednesday and over the past week we had the pleasure of getting to know Tara Cunningham, the Director of Strategic Planning for The Jay and Linda Grunin Foundation. Tara is a hands-on and dedicated woman who is devoting her time and effort towards creating a positive social impact within the Township of Toms River, New Jersey. 


Tara Cunningham

Tara Cunningham, Director of Strategic Planning

Get To Know Tara:

Tara Cunningham is an Ashoka Fellow and an internationally recognized, award-winning CEO and Social Entrepreneur.

Over the past 15 years, Tara has been appointed to various non-profit and governmental boards, advised non-profits, corporate social responsibility programs, social enterprises, government agencies, the European Commission, politicians and philanthropic foundations throughout the United States and Europe on how to create sustainable social impact. Tara joined the Jay and Linda Grunin Foundation in July 2014 and has used her experience to help the Foundation and its grantees create the greatest social impact. Tara lives in Toms River with her husband Mark and their children Eoin, Charlie and Emilia.

Board Directorships include:
• Trustee of Garden State Concerns of Police Survivors and Navy Lakehurst Historical Society
• Board Member of the Jersey Shore Chapter of the American Red Cross
• Inaugural Advisory Board Member of Ocean County College 100 Women
• Appointed member of the Ocean County Economic Development and Tourism Advisory Board and is an Honorary Commander at the Joint Base Maguire Dix Lakehurst.


1. Tara, I know our readers would love to know, in your own words, what drew you to working as the Strategic Planning Director at The Jay and Linda Grunin Foundation?

In 2013, I moved back to Toms River from Ireland where I lived for 16 years. I quickly got involved in the community and was appointed to the Ocean County Economic Development and Tourism Advisory Board where I met Jeremy Grunin. During our first discussion we talked about what he was trying to achieve and to my typical form, I challenged his approach. Instead of being put off by my bluntness I was invited to meet with the family to discuss how I felt I could help them achieve a deeper and wider social impact. I found Jeremy, his mother Linda and father Jay shared an unparalleled amount of ethical fiber, a massive resilience and unwavering determination to elevate Toms River. I began working with them as a consultant to complete a strategic plan over 6 months and after an incredibly fulfilling time, I was asked to stay on as their Director of Strategic Planning. I get to work with people I admire and every day I can see where my input makes a positive contribution to our community. I’m living the dream.

2. Can you please describe what your role as the Strategic Planning Director at The Jay and Linda Foundation embodies…What are your main responsibilities and duties?

As Director of Strategic Planning for The Jay and Linda Grunin Foundation I develop and implement the strategic approach the Foundation takes with all of our awardees and programs. In short that means, I work with organizations to review their current and future capacity needs and help them get to the next level. This includes providing research and analytic support to determine the needs of each awardee; assessing the community for collaborative opportunities to enable community-wide strategic decision making; meeting with elected and community leaders to enable cross-pollination of ideas and implementing best practice from social enterprises and non-profits world wide for maximum social impact here in Toms River.

3. In 2014, Sheryl Sandberg launched a campaign to ban the word “Bossy” to empower girls to lead. How can women manage the perceptions around assertiveness or being labeled “bossy”, particularly when they are often judged more harshly than men?

“Bossy” I wish that’s the worst I’ve been called. I was raised to challenge authority; to always ask why and if the answer to why isn’t an acceptable reason, make a positive change; expect the best from myself and those around me; to be big enough to admit when I am wrong and strong enough to explain to someone else why I think they are; to learn from and share my mistakes; to always ask myself after every major interaction “what have I learned”; and most importantly – have fun when making the world a better place. I am raising my three children, Eoin, Charlie and Emilia with the same ethos. How I’m perceived as a woman doesn’t matter to me, how I’m perceived as a human does.

4. Was it hard being a woman and climbing your way to achieve your current position? If so, how did you overcome the challenges i.e. support from fellow co-workers, strong desire to succeed…? If not, have there been other women who have held your current position?

I never had a problem “being a woman” and “climbing”. I spent the last 15 years in the social sector which is female dominated. I never felt excluded from the good ol boy club, nor have I had any women try to hold me back. In fact, a former funder and now dear friend Deirdre Mortell, Co-Founder of The One Foundation has been my mentor (God love her) for almost a decade. I hope I’m half as useful to the people I have and will help along the way!

5. Have you mentored women throughout your career? If so, what are your three best tips for success?

I believe the greatest honor you can have is to have someone ask you for advice and come back asking for more. I try to follow what great mentors have done for me. 1. Listen. Really listen. 2. Share a similar failure or issue you have gone through, so they know they too can survive their latest challenge. 3. Don’t be insulted if they don’t take your advice and don’t rub it in when they come back saying they should have!

6. What is the best piece of advice you have ever received for your career?

Never try to cover up a mistake. Admit it, learn from it and don’t do it again.

7. What career advice do you give younger women who are climbing the ladder of success and trying to manage life/work balance?

As true as there is no such thing as “happily ever after” there is absolutely no such thing as “work life balance.” It’s work life integration I strive for. If you try to balance, you’ll fail. But if you learn to integrate the two and put boundaries around time, you can manage to have both a successful career and a life.

8. What were some moments when you felt treated differently because you’re a woman?

Mark, at the time my new Irish boyfriend and now husband thought I didn’t know rugby because I was a girl. Not only did I know rugby, but I analyzed the plays a heck of a lot better than he did. I still do by the way. LOL. 🙂

But in all honesty, in work I never felt I was treated differently. I have never walked into a room feeling I was somehow inferior because I was a woman, so I guess that translated into being treated no differently than a man. 

9. What are important lessons around the topic of women and leadership for you?

Women need to stop waiting for everything to be 100% before they jump for a big promotion, raise etc. I have watched women sit out on tremendous opportunities because they didn’t have one skill, and the man who got the job didn’t have three of them. Put your name out there, expect you can achieve something, achieve more and expect to be paid at the top of the pay scale. Women are paid less because we demand less. It’s our fault ladies. STEP UP.

10. What’s unusual about the culture of the Jay and Linda Grunin Foundation?

Culture of the Jay and Linda Grunin Foundation is one of open, honest discussion and full transparency. There is huge integrity in our approach with each other which I believe cascades over into our work with our awardees. It’s pretty fantastic.

11. If you were to receive an award for, “Best At ____”. How would you fill in the blank and why?

“Drama”. Everyone who knows me knows every decision I make or hear about goes on the risk list. I analyze how that decision could cause a negative impact which is typically exaggerated beyond possibility. I find that drama / scenario planning enables me to make the best strategic decisions and catch problems before they hit. I also find it drives people absolutely crazy. Sorry!

12. What role does social media play in your role?

Our Foundation is so involved in the community we get over 1500 unique visitors to our website a month. We realized if we had a more interactive site coupled with excellent social media, we can help our grantees gain visibility and then hopefully additional funding and strategic partners. To that end we recently launched our new website, Facebook and Twitter pages. In our first day we had over 500 friends. We’re pretty excited to test the boundaries for our awardees and partners.

13. What do you believe is at the root of any good strategic plan?

These quotes from “Good Strategy Bad Strategy” by Richard Rumelt hang over my desk.

“Strategy is at least as much about what an organization does not do as it is about what it does.”

“Universal buy-in usually signals the absence of choice.”

“Strategy is primarily about deciding what is truly important and focusing resources and action on that objective. It is a hard discipline because focusing on one thing slights another.”

“Focusing efforts on fewer, or more limited, objectives generates larger payoffs.”

“Shift your attention from what is being done to why it is being done, from the directions chosen to the problems that these choices address.”

14. What was the “Aha” moment or turning point in your life that had a direct impact on your career and leadership?

I was working in advertising as the Interim Director of OgilvyInteractive in Dublin while volunteering five hours a week with terrific kids aged 9-14 in the inner city’s Clongowes Youth Club. Over a pint of Guinness I told Mark, my then boyfriend now husband, that I enjoyed my few hours a week with the kids more than my real job. He said, “Well why don’t you use your powers of evil for good and work in the non-profit sector.” So I did. That was the best thing I could have ever done.

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